


Never Have I Ever

by Ladywordsmyth



Category: Supernatural
Genre: Embarrassment, First Kiss, Fluff, Fluff and Humor, Goofy Dean Winchester, M/M, Men of Letters Bunker (Supernatural), Protective Dean Winchester, Tooth-Rotting Fluff, Wincest - Freeform
Language: English
Status: Completed
Published: 2020-01-18
Updated: 2020-09-01
Packaged: 2021-02-27 13:48:54
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 3,146
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22308208
Author URL: https://archiveofourown.org/users/Ladywordsmyth/pseuds/Ladywordsmyth
Summary: In a desperate attempt to relieve some stress about Chuck, the three boys decide to spend the night drinking and playing a harmless game of Never Have I Ever. As it is with many other "harmless" things, the night takes a different turn than expected.
Relationships: Dean Winchester & Sam Winchester, Dean Winchester/Sam Winchester
Comments: 20
Kudos: 102





	1. First comes Whiskey

**Author's Note:**

> Bunker life fic set during season 15 after Jack and Rowena's deaths. Fyi, this will become a clear wincest story so if you aren't into that, beware. Oh and also, a few spoilers

"Dean...come on. This is ridiculous. Why are we doing this?" Sam muttered, whining a little.

"What game is this?" Castiel asked. He took a delicate sip of whiskey, his nose scrunching up at the flavor.

"The game is called 'Never Have I Ever.' The _point_ , Sammy, is that it's _fun_ and I want to. We have been running ourselves ragged, man, we deserve a friggin break."

Sam couldn't exactly fault Dean's logic. It was true. After Chuck had resurrected all the monsters they had collectively killed, it was a mad dash to put them down as quickly as possible.

It had been a rough few weeks, certainly. The deaths of close friends, lack of sleep, on the job injuries, eating mostly fast food, long drives...the stress of it all was definitely taking a toll on everyone. Even Cass. As for the Winchesters, they were snapping at eachother and rarely spoke of anything other than Chuck and Monsters. Both brothers missed the comraderie they shared in their early years; hanging out together; having fun, laughing, drinking and playing pranks.

The loss of the closeness Sam and Dean usually had was jarring for each of them but in very different ways. Dean, not one for talking usually, missed the easy silences between them. It was almost telepathy the way they were able to convey thoughts with only a glance or a gesture.

Sam would never admit it out loud, but he missed the way Dean would care for him, almost like he was a kid again. In Dean's own way, he was a pseudo-parent to Sam who never knew his mother growing up, and had a father who was largely an absentee drill instructor. Despite Sam fighting for his independence as a young adult, he missed having Dean hovering, almost too close, looking after him. Sam knew it was sick, that longing but he knew himself well enough to admit he still wanted it fiercely.

Things had changed recently, and the need for normalcy had clearly lead Dean down a reminiscent path. Sam and Cass shared a look, finally understanding that what Dean wanted was to slow down for a moment. Cass nodded slightly to Sam and he silently agreed, their lives appearred to be spiralling out of control and neither Sam nor Cass could begrude Dean this one thing.

"Fine. But we need more whiskey," Sam grumbled.

" _Atta_ boy, Sammy!" Dean's smile was worth it. His face lit up like the field the boys had nearly burnt down on the Fourth of July all those years ago. That memory brought the sweetest ache to Sam's heart and he returned Dean's blazing grin.

Dean poured everyone a healthy amount of amber liquid into their glasses, leaving the bottle on the table for easy refills.

"Since this was your idea, do you want to go first?" Sam was feeling generous and slightly nervous about where to start.

"Fine, yeah. Ah...never have I ever... shit my pants at the amusement park," Dean deadpanned.

" _What the fuck_ , Dean?! _Why_ would you bring that up again?" Sam flushed, embarrassed despite that memory having been from nearly 20 years ago.

"Come on Sammy, you gotta drink. Them's the rules," Dean stated, forever smug.

Sam swallowed a mouthful of his whiskey, hoping the burn in his throat would help the shame staining his cheeks.

"Sam, That is awful...were you sick?" Cass cocked his head to the side, pity in his blue eyes.

"No, Cass I wasn't _sick_. Asshole over there wouldn't let me go to the bathroom before we went on the Zipper." Sam's eyes narrowed at Dean.

Dean laughed and leaned toward Sam at the table. "Oh shut up. It was not that bad. Poor Sammy had to go on the _amusement park ride_."

Sam gave his best bitch face. "No, Dean. You forced me to eat 2 corndogs and cotton candy like 10 minutes before that stupid ride! You are lucky I didn't upchuck on your damned shoes too!"

Dean slid back and barked out a laugh before leaning forward again. " _Poor little Sammy_ , if only he had a big brother who gave up his flannel to cover up the doody in his shorts. Oh wait, _I did do that_." Dean's eyebrows raised as though waiting for Sam to deny it.

Sam grumbled under his breath, but relented and changed the subject. " _Fine_ , my turn. Never have I ever...gotten so drunk I woke up in my own piss." There, Sam thought. Chew on that, Dean.

"Low blow, Sam! You know that only happened once!" Dean argued.

Sam wasn't willing to relent after Dean brought up the whole pants-shitting episode of his life.

"No way, Dean. It happened _twice_ and once there was even some bimbo in bed with you!"

Dean flushed red at that. His freckles stood out in strong contrast to the flush on his cheeks.

Cass watched them banter back and forth like it was a tennis match. He said nothing as the argument didn't much include him. He swirled his glass once and took a dainty sip.

" _Wait_. Cass, you know you only are supposed to drink when you _have_ done the thing, right? Like Dean over there should be drinking right now," Sam raised an eyebrow at Dean in challenge.

Dean gulped his drink, returning Sam's look. _There_ , his look said.

"Yes, I understand the game, Sam. When I was briefly human It happened to me once. I was new to the inner workings of my bladder and I didn't gauge correctly."

Sam snorted. "I guess that's a better excuse than Dean's."

Dean kicked Sam's chair under the table. Sam simply smiled.

____________________________________________

After a while, the boys cajoled and joked with eachother, successfully loosening their lips and inhibitions. As things often go, the questions got more sexual the more alcohol was consumed.

Sam found he was surprisingly enjoying himself. Despite all their other worries, being in the bunker drinking with the two closest people in his life, he finally relaxed.

"Oh, I have one. Never have I ever... accidentally walked in on my mother mid-coitus." Cas looked at both Sam and Dean respectively.

"That's not fair! You don't even _have_ a mom, Cas! _What the hell_?!" Dean's face scrunched up, looking vaguely sick.

Sam raised his glass to his mouth and drank sullenly as though wishing he could erase the memory with drink. He secretly hoped no one would notice but no _fucking_ luck. Dean's eyes widened in shock.

"No... _oh god_ , Sammy...you _didn't_... _please_. tell me you _didn't_."

Sam refused to look at Dean and simply poured himself more whiskey.

"Ick...that's so... _oh god,_ yuck! Wait. Who the _hell_ was she with? Bobby? Dad? Who the fuck...wait, _no_ , don't tell me..." Dean nearly whined.

"I refuse to answer anything about it. As far as I'm concerned it _did not_ happen. Got it?"

Dean was stunned and found himself guzzling his drink trying to bury this new information with more whiskey. He quickly poured more for Sam sympathetically.

To be continued...


	2. Next comes love

**Summary for the Chapter:**

> The boys grapple with the elephant in the room while Cass is a willing observer to the truth newly emerging.

A few moments ticked by as the Winchester brothers attempted to drink the information about their less-than-saintly mother out of their minds. Unfortunatley, they were only marginally successful and had mostly just succeeded in becoming more drunk. 

Sam was desperate to change the subject and since it was his turn, he went.

"Never have I ever, had sex with another guy."

Dean looked a little surprised that anyone had spoken and then, even more surprised at Sam's statement. Apparently, Dean had expected Sam to have been a lot more experimental in college. _Interesting_.

Cass sipped his whiskey, swirling it lightly in the glass.

" _Oh_. My. _God_. High and mighty actually got down with another dude?!" Dean looked almost gleeful at that.

Cass frowned. "Dean. You should realize by now that heaven did not create the social stigmas of earth. Humans did. Heaven has no distaste for any same-sex unions. And I confess to having been curious." Cass continued to sip his drink and appearred unembarassed.

Sam had to admit to a bit of surprise on his end as well. However, he was more surprised that _Dean_ hadn't tried it. Dean liked sex in _a lot_ of different flavors and had certainly had opportunities to experiment with his own gender. On more than one occassion, a guy had hit on Dean at a bar and a couple times Dean had looked at the potential bedpartner with an assessing eye. 

Sam had certainly considered it himself. And truthfully, _yeah_ , it had been at Stanford for the most part. He had considered it on more than one occassion after college as well, but something always stopped him from following through. It just never felt... _right_. Wrong _time_. Wrong _person_.

And with that particularly unhelpful thought... Sam turned to Cass.

"Your turn, Cass." Sam's voice held firm but still sounded pitchy to his own ears.

He looked at Dean briefly, hoping he hadn't noticed. Dean noticed, because _of course_ he had. He kept his mouth shut but continued to stare at Sam with laser focus. Sam swallowed and looked away.

Cass, normally not the most observant "person" in the world, still knew something was up but being well acquainted with the Winchester's avoidant ways, he chose not to comment.

"Never have I ever... had a sex dream about someone in this room." Cass smiled boyishly.

"That's such bullshit, Cass. We both know you barely need to sleep and as far as I know you don't dream about anything...let alone _sex_." Dean grumbled.

Cass just continued to smile and waited for the boys to admit to anything.

This was a bit of a loaded statement as Sam had had sex dreams about _both_ men in the room. One of the men was a frequent sex partner in his dreams but he was not willing to admit to which man that was. Sam lifted his lips to his drink and sipped, darting his gaze to his brother quickly.

Dean had his drink to his mouth as well, his lips barely grazing the rim of the glass. His gaze was latched onto Sam, his mind clearly assessing Sam's own. Sam's mouth went dry and he glanced away quickly, not sure what Dean's glance had _meant_.

More confused than ever, he drank his whiskey with his heart beating wildly. He kept his gaze fixed on his glass and the amber liquid within as though certain that it held all the answers to the universe.

He could feel Dean's eyes on him the entire time. It was maddening. Stubbornly, Sam refused to look up right away, afraid of what answers he would find in Dean's expressive eyes. Even more than that, Sam worried his brother would see the guilt in his soul for his unnatural feelings.

Sam hated to admit it but he had the worst poker face of all the Winchester boys. His brother and father had always been able to tell when he had done something wrong. The decades had not improved his skills so he was terrified that Dean would see straight through him to all the dark places inside his mind.

Cass cleared his throat and stood. Sam and Dean broke out of their stupors and looked up at the angel.

"Well boys, I think I've had enough for the night. Goodnight." He smiled thinly and placed his empty glass on the table.

" _Wait_ , Cass, where are you..." Sam began but the angel had already disappeared with a flutter of wings.

"I hate it when he does that." Dean sighed.

Sam swallowed, panicking slightly. He was now stuck in an empty room with the person he loved the most in the world, who he was pretty certain knew it. _Shit_.

To be continued...

**Notes for the Chapter:**

> Thank you for your continued interest in this story. The reason for this last installment is largely thanks to you guys so thank you for keeping me on track!


	3. Then comes marriage?

**Summary for the Chapter:**

> Sam and Dean have a heart-to-heart that brings the childish games full circle.

The tense silence between the brothers stretched out much longer than was normal for them. Silence wasn't unheard of for the Winchesters but it was never filled with so much unsaid. The distance between Sam and his brother seemed to stretch out further the longer they refused to put words to inner thoughts. Dean cleared his throat and jiggled his glass, a nervous tic Sam was well aware of.

Sam wanted to quit staring at the table or at the drink in his hand but his inner panic had him largely immobilized from looking up into the eyes who always managed to see too much. He worried that his expressive eyes would tell Dean everything that Sam was unable to voice aloud.

You see, Sam never meant to fall in love. He certainly never meant to fall in love with possibly the worst romantic prospect he had ever met, save _himself_ , that is. Even if he somehow hadn't been related to Dean, there were still a lot of reasons they shouldn't be together romantically. For one, his brother was almost annoyingly heterosexual. And lastly, Dean was almost as emotionally uninvolved as he. Needless to say, it all added up to a "no chance in hell" type of situation.

Sam sighed aloud unintentionally at his most recent revelation.

"What is it, Sammy?" Dean leaned in, worried.

Sam swallowed and reached for a smile to reassure Dean. It didn't come. The earlier teasing flirting had drifted away at Castiel's disappearance and now he was feeling rather melancholy. Sam prepared himself to offer his brother some useless platitudes but that wasn't what came out when he went to speak.

"Do you ever wonder if we are too broken to ever be happy?"

Dean cocked his head slightly and instead of teasing Sam for being broody, he answered thoughtfully.

"I don't know, Sam. Up until now it's always felt like no matter what we do, we aren't happy in every possible way. You know, when you were in the cage and I was with Lisa, I was probably the unhappiest I've ever been. I would rather be hunting and fighting everyday with my brother than romancing some chick. Don't get me wrong, I loved her as much as I could but I don't know if there is ever going to be a girl that could deal with what we do every day... it seems a bit unrealistic, you know? _Why_ , Sammy, what's going on in that big brain of yours?" Dean refilled their glasses with more whiskey and waited as Sam pondered his answer.

"I just wonder if time has run out for us. What if Chuck ends the world tomorrow...won't you feel like you missed out? That you never got to have the love of a partner who truly knows you? As much as I loved Jess and Amelia... they never knew all of me. I know that's my fault but as much as I loved them both I couldn't give either of them everything and now I feel like time is running out for me to ever have that kind love. I know that sounds stupid but..." Sam shrugged his shoulders and sipped his whiskey, his eyes on his glass.

Sam noticed Dean lean forward in his periphery but the alcohol and conversation were making him feel numb inside so he didn't even look up.

A calloused hand snuck out carefully and grasped Sam's, yanking his gaze to Dean's earnest green one. A line appearred between Dean's eyes and it was a look Sam recalled from childhood from when Dean would clean up his scraped knees or wipe away Sam's tears. It was an all focused concern that began to thaw the ice around Sam's heart.

"Look, Sammy, I know it aint ever been easy for either us in the love department but you should know that you have people around you who do know you. Really know you. And they...love you." Dean stated the last part somewhat nonchalantly despite the rasp in his throat like it had been dragged out of him coated in sandpaper.

Sam smiled weakly, his eyes welling. He tried to look away and snatch his hand back before Dean could tease him for being an emo girl but Dean held fast.

Sam looked up and licked his lips, mouth dry. Dean's eyes laser-focused on Sam's mouth and suddenly Sam's brain lit up with understanding and a loosely formed idea occured to him. The atmosphere had changed between them and so should the game. Worried he may never have another opportunity, he said "truth or dare?"

Dean blinked at the sudden change. He began to pull back but this time Sam gripped Dean's hand tight. Dean's eyes were shuttered again and he worried his lip between his teeth. Sam felt helpless not to stare, his mouth filling with saliva.

Dean watched the expression on Sam's face warp and become tense and needy. Dean's eyebrow cocked inquisitvely but falling back into old habits he complied, giving Sam whatever he needed.

"Dare." Dean's eyes flared in challenge and Sam finally smiled a real smile.

"I dare you to kiss me, Dean." Sam whispered, hoping against hope he was right and not about to majorly fuck up their relationship.

  
He held his breath when suddenly Dean surged forward. Propelled by Dean's hand urging him forward and by his own lust, their mouths met. Contrary to how Sam believed their first kiss might be, it was actually quite soft and exploratory. Dean's mouth was warm and moved languidly against his own. Dean's other hand, the one not clutching Sam's, reached to angle Sam's face nearer. Sam gasped and Dean's mouth swallowed the sound. Dean's kisses deepend and he coaxed Sam's mouth open so their tongues could finally touch. At the first wet rubs of Dean's tongue, Sam moaned. Dean pulled back slightly to nibble Sam's lower lip. Dean retreated and left Sam standing there, struck dumb. Dean's mouth curved into a smile usually reserved for busty waitresses and Sam blushed.

"Truth or dare, Sammy?" Dean's voice had gone gravelly and Sam shivered.

"Dare." Sam's own voice was shot, he cleared it and he tried to appear confident when he felt anything but. Dean's eyebrow rose in challenge, a small smile playing at the edge of his mouth.

"I dare you to take me to bed." Dean's voice was low and intimate. It had Sam shivering with arousal. He couldn't believe his luck but not one to look a gifthorse in the mouth, he tugged Dean's toward him and began leading them towards Sam's bedroom. Sam was sure he looked like a lovestruck teenager but he walked slowly, never taking his eyes off Dean, worried one of them might snap out of the trance and blame the alcohol.

Dean finally rolled his eyes and lead the way, past Sam's bedroom. An inquisitive sound escaped Sam then and Dean shrugged.

  
"my bed is memoryfoam. Much comfier." He winked and dragged Sam into Dean's bedroom and slammed the door, chuckling.

The end.

**Notes for the Chapter:**

> I'm so sorry it has taken me so long to finally wrap up this story but I haven't been writing much as my inspiration bunny has been sleeping. She nipped my ass today and I finally was able to finish off this little story for good. I hope you enjoyed it. Smooches.

**Author's Note:**

> Thank you for reading! Your comments and kudos are appreciated if not obligatory. Smooches ;)


End file.
